NEW HARLEY-DAVIDSON® MOTORCYCLE INVENTORY

Explore new 2025 & 2026 Harley-Davidson® models for sale at Windy City Harley-Davidson® in Libertyville, IL

Find your next new motorcycle when you work with the experts at Windy City Harley-Davidson^®! We offer a huge selection of hundreds of new bikes for sale, so we're sure to have something in stock to fit your riding needs!

Why Buy From Us?

Anyone can sell you a motorcycle. What sets us apart is what happens after. We believe in treating people like family, not numbers, and making sure every rider feels supported long after they leave the showroom. From service and parts to events and community, we’re here for the long haul — because your experience shouldn’t end when the sale does.

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Chicago Harley-Davidson®

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Windy City Harley-Davidson®

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Harley-Davidson® Heritage Softail® Classic 2017 FLSTC BLACK $11,999.00

034478

Pre-owned

2017

24500 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1BWV1XHB034478

Two-Tone Black Hills Gold/Black Quartz

The Heritage Softail® Classic is rich with the nostalgia of days gone by, but the hidden suspension gives you the authentic look of a hardtail without the bone-shaking ride. You get the comfort of standard cruise control and a low center of gravity, plus standard ABS, and a High Output Twin Cam …

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Harley-Davidson® CVO™ Street Glide® 2017 FLHXSE SF BLK/ATMC RED W/PINSTRIPE $37,799.00 $20,999.00

960559

Pre-owned

2017

23760 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1PXF18HB960559

Starfire Black/Atomic Red with Contrast Chrome Aggressor Wheels

The CVO Street Glide® is decked out fender to fender with custom details and our most powerful engine and sound system. The all-new black granite Milwaukee-Eight™ 114 engine is at the heart and when you unleash it at the light, hold on. The 6.5” BOOM!™ Stage II speakers are powered by two 300-watt …

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FXDF 2017 Fat Bob® $16,499.00 $9,999.00

308538

Pre-owned

2017

9088 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1GYM12HC308538

Crushed Ice Denim

Subtle is not the word that comes to mind when describing the Fat Bob®. Tommy Gun exhaust. A unique dual headlight and custom LED tail light. Fat rubber rolling on machined disc wheels. And performance that lets you get down to business with the Twin Cam 103™ engine and dual disc brakes. The look …

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FXDBP 2017 Street Bob® $9,999.00

323074

Pre-owned

2017

25348 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1GXM13HC323074

Black Denim

The original bobber fanatics invented the style, and they had one rule: if it’s not essential, get rid of it. That’s the Street Bob®. 103 cubic inches of Harley-Davidson® V-Twin power. Solo seat. Chopped rear fender. Mini-apes. Blacked out fork lowers and triple clamps, blacked out engine finish …

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FLTRXS 2017 Road Glide® Special $23,999.00 $18,999.00

652670

Pre-owned

2017

11548 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1KTC10HB652670

Velocity Red Sunglo

Those who appreciate the aggressive look and wind-cutting power of the frame-mounted shark nose fairing and dual Daymaker™ Reflector LED headlamps on the Road Glide® Special model wouldn’t ride anything else. And now the ride gets even more aggressive thanks to the all-new Milwaukee-Eight™ 107 …

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FLHXSE 2017 CVO™ Street Glide® $37,799.00 $22,995.00

954910

Pre-owned

2017

37171 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1PXF18HB954910

Starfire Black/Atomic Red with Contrast Chrome Aggressor Wheels

The CVO Street Glide® is decked out fender to fender with custom details and our most powerful engine and sound system. The all-new black granite Milwaukee-Eight™ 114 engine is at the heart and when you unleash it at the light, hold on. The 6.5” BOOM!™ Stage II speakers are powered by two 300-watt …

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FLHXSE 2017 CVO™ Street Glide® $34,949.00 $22,999.00

960361

Pre-owned

2017

32484 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1PXF19HB960361

Starfire Black/Atomic Red with Contrast Chrome Aggressor Wheels

The CVO Street Glide® is decked out fender to fender with custom details and our most powerful engine and sound system. The all-new black granite Milwaukee-Eight™ 114 engine is at the heart and when you unleash it at the light, hold on. The 6.5” BOOM!™ Stage II speakers are powered by two 300-watt …

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FLHXS 2017 Street Glide® Special $24,299.00 $15,999.00

657933

Pre-owned

2017

7033 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KRC15HB657933

Black Denim

The Harley-Davidson® Street Glide Special model set the world standard for the stripped-down, hot rod look. Its style is often copied, but never duplicated. The all-new Milwaukee-Eight™ 107 engine backs up the look with massive torque. The ride is unmatched as well, thanks to the all-new suspension …

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FLHXS 2017 Street Glide® Special $23,699.00 $15,999.00

680374

Pre-owned

2017

14561 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KRC10HB680374

Black Denim

The Harley-Davidson® Street Glide Special model set the world standard for the stripped-down, hot rod look. Its style is often copied, but never duplicated. The all-new Milwaukee-Eight™ 107 engine backs up the look with massive torque. The ride is unmatched as well, thanks to the all-new suspension …

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FLHXS 2017 Street Glide® Special $23,699.00 $17,999.00

652905

Pre-owned

2017

8914 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KRC18HB652905

Crushed Ice Pearl

The Harley-Davidson® Street Glide Special model set the world standard for the stripped-down, hot rod look. Its style is often copied, but never duplicated. The all-new Milwaukee-Eight™ 107 engine backs up the look with massive torque. The ride is unmatched as well, thanks to the all-new suspension …

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FLHTK 2017 Ultra Limited $23,299.00 $16,999.00

655382

Pre-owned

2017

34793 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1KED17HB655382

Two-Tone Black Hills Gold/Black Quartz

If you’re the kind who wants it all, the Ultra Limited gives it to you. From the powerful all-new Twin-Cooled™ Milwaukee-Eight™ 107 engine, right down to the heated handgrips. The unmistakable Batwing fairing and Splitstream air vent mean optimal air flow and reduced head buffeting. Premium BOOM!™ …

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FLHTCUTG 2017 Tri Glide® Ultra $35,539.00 $29,999.00

860258

Pre-owned

2017

8895 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1MAD18HB860258

Superior Blue

The Tri Glide® Ultra is everything you love about the Ultra Limited, only on three wheels. You get every feature and improvement starting with the power of the all-new Twin-Cooled™ Milwaukee-Eight™ 107 engine. Other touring features include a 4-speaker, premium BOOM!™ Box 6.5 GT infotainment system …

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